All Collections

8 properties

Cozy library nook with queen pull out couch

A private patio perfect for morning coffee or evening wine

Main-level king suite with private bath and direct patio access

Fully equipped kitchen with everything needed for home cooking

Upstairs queen bedroom with in-window AC for year-round comfort

Upstairs queen bedroom with in-window AC and TV

Cozy library nook with queen pull out couch

Private ensuite for a little extra ease and privacy

Open, inviting spaces designed for connection and conversation

Gather and enjoy ~ this dining space was made for it

A storybook exterior in one of Ashland’s most walkable neighborhoods

Texture and history in every corner

Full upstairs bathroom with tub

Downstairs half bath off the kitchen with laundry

First-floor king suite featuring a private covered patio and Smart TV

House

Ashland, OR

3 bedrooms 2 baths 8 guests

From $ 149.00 /night

Whimsy on B | 2BR + Studio Near OSF – Photo 1

Whimsy on B | 2BR + Studio Near OSF – Photo 2

Whimsy on B | 2BR + Studio Near OSF – Photo 3

Whimsy on B | 2BR + Studio Near OSF – Photo 4

Whimsy on B | 2BR + Studio Near OSF – Photo 5

Whimsy on B | 2BR + Studio Near OSF – Photo 6

Whimsy on B | 2BR + Studio Near OSF – Photo 7

Whimsy on B | 2BR + Studio Near OSF – Photo 8

Whimsy on B | 2BR + Studio Near OSF – Photo 9

Whimsy on B | 2BR + Studio Near OSF – Photo 10

Whimsy on B | 2BR + Studio Near OSF – Photo 11

Whimsy on B | 2BR + Studio Near OSF – Photo 12

Whimsy on B | 2BR + Studio Near OSF – Photo 13

Whimsy on B | 2BR + Studio Near OSF – Photo 14

Whimsy on B | 2BR + Studio Near OSF – Photo 15

House

Ashland, OR

3 bedrooms 2 baths 6 guests

From $ 199.00 /night

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 1

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 2

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 3

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 4

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 5

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 6

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 7

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 8

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 9

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 10

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 11

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 12

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 13

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 14

Peerless Hotel Honeymoon Suite 7 + Signature Rm. 6 – Photo 15

Other

Ashland, OR

2 bedrooms 2 baths 4 guests

From $ 199.00 /night

Primary king bedroom with fireplace, TV, and hot tub access

New 6 person hot tub overlooking the mountains

Large living room with TV, fireplace, and wraparound couch- space for the whole group!

Primary bathroom with large soaking tub, dual vanities, and walk in shower with dual shower heads

Covered outdoor fireplace

Farmhouse front entrance

Onsite pond- perfect for watching the ducks

Spacious farmhouse kitchen

Large wraparound couch

Upstairs queen room with valley views

Upstairs bunk bed room with twin over twin and trundle, and standalone full bed

Upstairs shared bathroom with dual sinks and large walk in shower with dual shower heads

Dining room with plenty of table extensions to fit everyone

Half bath off the dining room

House exterior

House

Talent, OR

7 bedrooms 3 baths 18 guests

From $ 299.00 /night

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 1

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 2

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 3

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 4

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 5

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 6

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 7

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 8

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 9

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 10

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 11

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 12

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 13

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 14

Grandview of Ashland | Hot tub | Sauna | Fire Pit – Photo 15

House

Ashland, OR

2 bedrooms 3 baths 6 guests

From $ 139.00 /night

Fully stocked gourmet kitchen with gas range

Bathroom with soaking tub and walk-in shower

Spacious open living room with smart TV

Primary queen bedroom

Full bedroom

Refrigerator and gas rage

Dining room with seating for 6

Kitchen with island

Family friendly games

Primary queen bedroom

Sitting area and dining room

Threshold from dining room to kitchen

Kitchen staples

Kitchen with microwave, dutch oven, and instant pot

Bathroom with walk-in shower

House

Ashland, OR

2 bedrooms 1 bath 4 guests

From $ 109.00 /night

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 1

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 2

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 3

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 4

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 5

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 6

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 7

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 8

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 9

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 10

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 11

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 12

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 13

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 14

The Peerless Hotel | Honeymoon Suite #7 | Private Jacuzzi | Mountain Views – Photo 15

Other

Ashland, OR

1 bedroom 1 bath 2 guests

From $ 129.00 /night

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 1

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 2

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 3

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 4

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 5

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 6

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 7

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 8

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 9

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 10

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 11

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 12

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 13

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 14

The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs – Photo 15

Other

Ashland, OR

1 bedroom 1 bath 2 guests

From $ 129.00 /night